Matteson Homologation-Based Total Synthesis of Meliponamycin A

Abstract

The first total synthesis of meliponamycin A, an antimicrobial cyclodepsipeptide isolated from Streptomyces, is reported. Two key building blocks, the substituted tetrahydropyranyl side chain and an azido analogue of protected βhydroxyleucine, were constructed via iterative Matteson homologations. A fragment coupling of a tetrapeptide, a depsidipeptide building block, macrocyclization, Staudinger reduction, and Nacylation are further steps in the synthesis.